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. Author manuscript; available in PMC: 2019 Nov 1.
Published in final edited form as: Prostaglandins Other Lipid Mediat. 2018 Oct 5;139:29–35. doi: 10.1016/j.prostaglandins.2018.10.002

Figure 3. Mechanism of IsoLG-adduct formation.

Figure 3

The aldehyde group of IsoLG spontaneously reacts with primary amines to form a highly reversible imine adduct (Schiff base). The 4-keto moiety of IsoLG subsequently reacts with the nitrogen of the imine, generating a dihydropyrrolidine adduct which then loses two water molecules to form the essentially irreversible pyrrole adduct. Under oxidizing conditions, this pyrrole